Asymmetric synthesis of a new cylindrically chiral and air-stable ferrocenyldiphosphine and its application to rhodium-catalyzed asymmetric hydrogenation

Kang, Jahyo; Lee, Jun Hee; Ahn, Sung Hoon; Choi, Jong‐Jin

doi:10.1016/s0040-4039(98)01089-2

Cited by 75 publications

(30 citation statements)

References 21 publications

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“…[1] Kürzlich haben wir C 2 -symmetrische Ferrocenylliganden vom Ferriphos-Typ 1 beschrieben, die sich bei der homogenkatalytischen Hydrierung von a-Acetamidoacrylsäurederivaten als sehr effizient erwiesen haben. [2,3] Nun stellen wir die chiralen Diphosphanylferrocenyl-Derivate 2 a ± d vor, mit denen sehr , 111, 1774Angew. Chem.…”

unclassified

Ferrocenylliganden mit zwei Phosphanylsubstituenten inα,ɛ-Position für die Übergangsmetall-katalysierte asymmetrische Hydrierung funktionalisierter Doppelbindungen

Ireland¹,

Großheimann²,

Wieser-Jeunesse³

et al. 1999

Angewandte Chemie

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unclassified

Ferrocenylliganden mit zwei Phosphanylsubstituenten inα,ɛ-Position für die Übergangsmetall-katalysierte asymmetrische Hydrierung funktionalisierter Doppelbindungen

Ireland¹,

Großheimann²,

Wieser-Jeunesse³

et al. 1999

Angewandte Chemie

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“…The MandyPhos family of ligands (32) have been used to reduce enamides to aamino acids as well as an enol acetate to produce an a-hydroxy ester [134][135][136][137][138][139][140]. The substituents R and R 1 can be used for the fine-tuning of a specific substrate.…”

Section: Ferrocene Ligandsmentioning

confidence: 99%

Enantioselective Alkene Hydrogenation: Introduction and Historic Overview

Ager¹

2006

The Handbook of Homogeneous Hydrogenation

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23Enantioselective Alkene Hydrogenation: Introduction and Historic Overview Development of CAMP and DIPAMPDuring the late 1960s, Horner et al. [13] and Knowles and Sabacky [14] independently found that a chiral monodentate tertiary phosphine, in the presence of a rhodium complex, could provide enantioselective induction for a hydrogenation, although the amount of induction was small [15][16][17][18][19][20]. The chiral phosphine ligand replaced the triphenylphosphine in a Wilkinson-type catalyst [10,21,22]. At about this time, it was also found that [Rh(COD) 2 ] + or [Rh(NBD) 2 ] + could be used as catalyst precursors, without the need to perform ligand exchange reactions [23].Knowles found that the monophosphine CAMP (1a) could provide an ee-value of up to 88% for the reduction of dehydroamino acids. CAMP was an extension of PAMP (1b) that provides ee-values of 50-60% in analogous reactions [24]. At this time, Kagan showed that DIOP (2) (vide infra), where the stereogenic centers are not at phosphorus, could also provide enantioselective induction in an hydrogenation. DIOP also showed that a bisphosphine need not have the chirality at phosphorus, and that good stereoselectivity might result from a C 2 -symmetric ligand. Knowles then developed the C 2 -symmetric ligand DIPAMP (3) [22,25]. The use of Rh-DIPAMP for the synthesis of l-Dopa is well known and is still practiced today [12,22,27]. A number of variations of the DIPAMP structure were investigated for the synthesis of this important pharmaceutical, but the parent remains the best ligand in this class [22].

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“…Bidentate derivatives of ferrocene, cymantrene, and some tricarbonyl complexes of chromium and rhenium have been actively investigated and demonstrated from good to excellent enatioselectivity in asymmetric hydrogenation, allylation, hydrosilylation and conjugate addition (for example, see [1][2][3][4][5][6][7][8]). Despite the encouraging performance of many bidentate ligands, especially phosphines, recent breakthroughs have shown that the use of bidentate ligands is not essential to obtain high enantioselectivity.…”

Section: Introductionmentioning

confidence: 99%

Cymantrene-derived monodentate phosphites: New ligands for Rh-catalyzed enantioselective hydrogenation

Lyubimov¹,

Davankov²,

Loim³

et al. 2006

Journal of Organometallic Chemistry

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Asymmetric synthesis of a new cylindrically chiral and air-stable ferrocenyldiphosphine and its application to rhodium-catalyzed asymmetric hydrogenation

Cited by 75 publications

References 21 publications

Ferrocenylliganden mit zwei Phosphanylsubstituenten inα,ɛ-Position für die Übergangsmetall-katalysierte asymmetrische Hydrierung funktionalisierter Doppelbindungen

Ferrocenylliganden mit zwei Phosphanylsubstituenten inα,ɛ-Position für die Übergangsmetall-katalysierte asymmetrische Hydrierung funktionalisierter Doppelbindungen

Enantioselective Alkene Hydrogenation: Introduction and Historic Overview

Cymantrene-derived monodentate phosphites: New ligands for Rh-catalyzed enantioselective hydrogenation

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